


Good girl

by The_mykie_show



Series: Tumblr requests and prompts [10]
Category: The Walking Dead & Related Fandoms, The Walking Dead (Comics), The Walking Dead (TV)
Genre: Anal Play, Anal Plug, Anal Sex, Ass Play, Daddy Kink, Dirty Talk, F/M, Praise Kink, Vaginal Fingering
Language: English
Status: In-Progress
Published: 2019-02-20
Updated: 2019-02-26
Packaged: 2019-11-01 11:33:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,781
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17866484
Author URL: https://archiveofourown.org/users/The_mykie_show/pseuds/The_mykie_show
Summary: When Negan finds a box of anal plugs on a run he knows exactly whose ass he wants to fill.





	1. First time for everything

**Author's Note:**

> This was originally going to be a one-shot for a Tumblr request but I had so many ideas for this one and so many kinky directions I could take this I decided to make it into a mini series.

“Daddy’s home!” Negan loudly announces as he kicks open the door to the lavishly furnished room where his wives spent their days. His hands are full of a large box, you would assume it was probably lingerie or liquor, or some other unnecessary luxury item that he found on a run and gave the women he called his first pick of. You rarely ever took things that you didn’t really need from the little gifts Negan brought, after all you hadn’t agreed to be his wife for the perks like most of the other girls had, you actually liked Negan, and enjoyed being with him, in more ways than one. But this time Negan doesn’t give you much of a choice, “Y/N, I have a little something to discuss with you.” he beckons you into his room, sitting the box down on his desk before pulling you to him and giving you a rough kiss. 

“What’s with the box?” you ask. 

“See for yourself.” he watches with with his signature smirk as you open the box and examine the contents, it’s filled to the brim with sex toys of all shapes and sizes, some are your run of the mill dildos and vibrators, but others are kinky things like handcuffs or gags. But most of the box is filled with smaller, almost oval shaped toys. 

“You want to use these on me?” you ask, Negan nods, confirming your suspensions. 

“What are these?” you ask holding up one of the smaller bulbous toys. 

“They’re sex toys.” Negan says in a deadpan tone. 

“I know that, asshole!” you retort, “I meant what kind? What do they do?” you continue to examine the toys, they start small and go up in size, some are solid metal, others are metal coated in silicone rubber, some are just rubber. Most have small jeweled hilts on them, but some have long furry tails, a few of them even look like they vibrate. 

“Most of them are plugs, you uh… put them in your ass.” he explains, awkwardly rubbing the back of his neck, waiting for your response. 

“And the first person you thought of for this is me? Do I give off some I want to be fucked in the ass vibe or something?” truth be told you are curious how it would feel. 

“No,” he laughs “I just remembered when you first agreed to be my wife you told me that you aren’t opposed to the idea of having your ass fucked, so I thought you might be open to a little anal play. Of course you don’t have to, you never have to,” he explains. 

“I don’t know… I mean I guess I am curious about it, but it seems a bit uncomfortable. Won’t it hurt?” you asked, this would be the most awkward conversation of your life if it was with anyone but Negan. 

“Uncomfortable, maybe a little at first, but it definitely shouldn’t hurt. Not if we it do it right.” 

“Do you..?” you gestured to the box of sex toys vaguely. 

“Know how to do it right? Yeah. You know I wouldn’t hurt you, babygirl.” he reassures you, his fingers softly touching your cheek. You do know that, he would never hurt you intentionally, but looking at some of the bigger plugs makes you feel like unintentionally hurting you is a very high possibility. 

In the end your curiosity wins.

“Could we just start with a small one?” you ask sheepishly. 

“That’s the idea, yeah. You have to work your way up.” Negan goes through the box of toys until he finds the smallest plug, a little black one that’s covered in silicone rubber and has a bright pink jewel on the hilt of it, and pulls a bottle of lube out of a drawer in his nightstand. 

He sits on the bed and pulls you down next to him, unzipping your dress and slipping it down to bunch around your waist, leaving you in the pink and black lace bra you had on under it. 

“Now let’s you get you nice and turned on,” his hands start to message your shoulders, and you feel his lips against the back of your neck. You instantly lean into his touch, feeling yourself relax into the familiar sensations. 

“There you go, just relax, let me make you feel good.” his hands slide lower, unhooking your bra and slipping it off while his lips work against the sensitive skin on the back of your neck. He gently lays you down against the bed, planting soft kisses down your breasts before taking your nipple between his lips and sucking it into a hardened peak, before moving on the other nipple and doing the same. 

By the time he’s done you’re already wet and moaning. 

“that’s my good girl, always so sensitive to my touch.” he pulls your dress all the way off, with your panties. “Open your legs baby, let daddy see how wet you are.” you do as he says, moaning when he strokes your slit with his thumb, you think he’s going to slip his fingers inside you and fuck you until you come around them, or he’s going to bend down and lap up your wetness, but he does neither. Instead he keeping playing with your clit, “Damn baby, you’re so wet, I bet that little pussy is just aching to be fucked, huh?” 

“Yes, please daddy!” you whine. 

“Sorry babygirl, you don’t get to come until that tight little ass is plugged.” he grabs the lube and the plug off the bed behind him. 

“Bend over my lap, just like you do when I give you spankings,” you can feel your pussy absolutely drip with need, and you immediately bend over his lap, exposing your ass to him. 

You get a little nervous again when you feel his hand start to rub your ass, and he spreads your cheeks. 

“Negan, I’m scared.” you admit. 

“Don’t be honey, I’ll take good care of you. It’ll feel good, trust me.” 

You nod slowly “Okay, just be gentle?” 

“I will be, just relax.” you hear him open the lube. “I’m just going to put a little lube on you,” you feel a drop of cold thick liquid fall between your ass cheeks. Some of it runs down your folds, making you feel wet and slippery between your thighs, you can also feel it settling in your puckered entrance. 

You turn your head and watch Negan lube up the plug. 

His hand spreads your ass cheeks, and you feel the tip of the plug against you. 

“I’m going to slide the plug inside you, okay?” 

You nod and feel him slowly press down. 

“Just relax, let daddy take care of you.” he says reassures you as you feel pressure inside your ass, it stretches you in the strangest way, it doesn’t exactly hurt, but it isn’t comfortable either. 

“Good girl, you’re taking it so good,” he praises you,knowing very well what that does for you. 

You whimper when you feel the largest part of the plug sliding in. 

“Look at you, letting daddy fill your ass. You’re such a good little girl.” he massages your ass cheeks once the plug is firmly placed inside you. 

“daddy,” you whine “its uncomfortable.” 

“I know, you’re not use to it, the first time you get your ass plugged is always a little uncomfortable. We can stop if you really want, but it’ll feel so good once you come around it.” he assures you. You nod, agreeing to let him leave it inside you. 

“That’s my dirty girl.” his hand finds your clit, his fingers began to rub slow circles around the sensitive bundle of nerves, making your core clench. 

“Oh!” you moan in surprise, clenching around the plug feels so strange and foreign, but you kind of like it. 

Negan keeps up the circles around your clit until you feel the coil of pleasure building in your core, making you clench tighter around the plug. You rock your hips against his hand, the intensity of your orgasm surprised you when it came. 

“Oh my God, Negan!” you moan, gripping the sheets when you feel your ass squeezing the plug with each spasm of your orgasm. 

“Good girl, come for me,” he keeps rubbing your clit while your body spasms with pure pleasure. Once your orgasm subsided into aftershocks Negan’s hand stopped rubbing your clit and moved to massage your ass cheeks 

“Holy shit….” you whimper, Negan’s massaging is causing the plug to move and press further into you ass, it feels strange but you find that you like it. 

“Does it feel good?” he asked. 

“Yes.” you moan.

He spreads your ass checks, rubbing his thumb against the jewel. “You look so pretty with your ass filled and that sweet little pussy dripping for me.” you feel him gently turn the plug inside you making you squirm. 

“Alright baby, I’m going to pull it out now.” he tells you, you feel the plug slowly slide out, it’s an oddly satisfying feeling, but leaves you feeling so empty once it’s out. You can feel your ass clenching as if it’s still there. 

“You can get up whenever you’re ready.” you slowly stand, you aren’t used to the wet, freshly fucked feeling in that hole. 

You flop down on the bed next to him. 

“Wow…” you groan. 

“You really liked it?” he asks, bending down and kissing you gently. 

“Yeah, I did. It felt weird and a little uncomfortable at first, but once I got used to it I liked it.” 

“So you want to do it again?” you nod. 

“Shit like this is why you’re my favorite, none of the other girls let me put so much as a finger their ass and here you are letting me train you with plugs and enjoying the fuck out of it.” you know it’s probably strange that you’re touched by him saying you’re his favorite in this context but you are nonetheless. 

“Go clean yourself up babygirl.”


	2. Part 2

**Summary for the Chapter:**

> You find out your body can do something you never thought possible after you and Negan experiment with the anal plugs that he found on a supply run.

From that point on Negan bends you over his lap several nights a week and plugs your ass, making you come with his fingers, eventually you find yourself even enjoying the feeling of having the plug inserted which was so uncomfortable for you the first time.  
You finally feel ready to insert the plug yourself on the forth night.  
“Come bend over babygirl.” Negan says sitting down the edge of the bed in your normal position.  
“Actually…” you say sheepishly “I was thinking I could try doing it by myself tonight.”  
“Really? If you're sure, as long as I get to watch.” he hands you the plug and the lube. “Tease yourself a little bit before you try, just like I do to you.” he instructed.  
You nod, leaning back against the pillows and letting your hand glide down to your core, your fingers circle your clit.  
“Fuck I am a lucky man.” Negan leans against the bedpost watching you play with yourself. Once your wet enough you slipped your fingers inside your entrance, fingering yourself until you feel like you're on verge of orgasm. You force yourself to stop, and spread your legs a little wider,taking the lube and putting a drop of the cool liquid against your hole, and then coated the plug in a generous amount.  
You press the tip against your ass, it doesn't feel good this time, in fact it hurt. You try again, whimpering, but this time it isn't in pleasure.  
“Does it hurt?” Negan asked. You nod. He takes your hand slipping the plug from your fingers.  
“You're still new to this, just let daddy take care of you.” he puts some more lube on the plug, but you find your legs closing on their own accord. You feel embarrassed and self conscious. You can't look Negan in the eyes.  
“What's wrong baby?” he asked before realization dawned on him. “There's nothing to be ashamed of, it's not a big deal. Just open your legs, it's always harder when you try using a new position.” you finally do as he says and spread your legs open wide, giving him access.  
With the fingers not holding the plug he rubs your clit, and with the other presses the plug against you.  
“Just relax.” he reassures you, as he presses the plug in, his fingers still working your sensitive bundle of nerves. The combination is a whole new level of pleasure, a soft surprised moan falls from your lips.  
“That feel good?” you nod. With his thumb still rubbing circles around your clit the tip of his index finger teasing your entrance, making you whimper with need. He slowly pushes it inside you, your body involuntarily clenching around it, he withdraws it and adds his middle finger. You feel so full, it's incredible. His thrusts get more and more intense, your thighs start to clamp around his wrist, your hips bucking to meet his hand. His fingers work that little spot deep inside you that he's always been so good at finding, while the plug rubs against something even deeper inside you. The fullness you feel is unreal, combined with the friction its downright orgasmic.  
“Shit darlin’ you're even tighter like this. Can't wait for it to my dick you're clenching around.” you feel a little naive to have not realized before this that one of the end goals of using the plugs was for him to fuck you with one inside, but you're not mad at the idea. If it feels half as good as this you're definitely down for it.  
You can feel your orgasm building, each stroke of his fingers pushing you closer to the edge, and when you finally find your release its most intense orgasm you've ever had.  
You want to scream in pleasure but no sound will come out, your eyes roll back in your head, and your legs shake, your hands twist in the sheets under you, hanging on for dear life. Negan's fingers work you through your orgasm, it lasts longer than any other you've ever had, and takes your breath away. When you crest what you're sure will be the final wave of your pleasure something new happens, you feel a warm rush between your legs, and your walls clench harder than ever. Your back arches off the bed and the scream you couldn't get out before finally released, your vision went black at the edges with the intensity of the pleasure you feel.  
Negan looks surprised but pleased, letting his hand work you until the warm gushing feeling subsides and your body relaxes around his fingers. When he pulls his hand from between your legs it's soaked all the way to his wrist, and you realize you're also soaked, and so are the sheets under you.  
“What just happened?” you feel drunk.  
“You squirted, babygirl.” he says “and now that we know you have that in you things just got a lot more interesting.” his signature smirk spreads across his face as he reaches between your legs and pulls the plug out making you moan softly again. You feel so wet, but it's different then just the wet, freshly fucked feeling that the plug always leaves behind, more intense somehow.  
“I made a mess.” you observe, your face heating up with embarrassment.  
“Shit honey, that was hot as fuck, knowing that I made you feel that good, you don't have anything to be ashamed about.” you nod, still feeling awkward as Negan gets up and gets you a towel to clean yourself up with. Although you're pretty sure you'll need a full shower to get all the slightly sticky leftovers from your orgasm off you, and Negan's sheets will surely have to be washed.  
Negan leans over you, planting a soft kiss on your lips, you return it lazily and it hits you how tired you are. A yawn over taking you as soon as he pulls away.  
“Did I wear you out?” he asks.  
“Yeah, I guess you did. That was… wow.” you admit, too tired to move as you watch Negan cleaning up the remaining mess, and putting away the lube. “I didn't even know that was something I could do.”  
Before a week ago you never thought you'd be saying this, but you were damn happy you gave the plugs a chance.  
“I told you that you'd love it.” he says as if he'd read your mind. “So you'll let me do that again?” he looks like a kid in a candy store when you nod eagerly before drifting off into a restful sleep.


End file.
